Hydrochloric Acid → HCID 11482987, compound

HRID 254164Notes

Reaction equation

HRID 254164 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[N:13](COCC[Si](C)(C)C)[CH:14]=[CH:15][N:16]=2)=[O:9])[CH:5]=[C:4]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)[N:3]=1.Cl>CO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[NH:13][CH:14]=[CH:15][N:16]=2)=[O:9])[CH:5]=[C:4]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59022910HCID 59022910, compound

Product 1

HCID 11482987HCID 11482987, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-amino-6-(2-furyl)-N-(1-(2-(trimethylsilyl)ethoxy)methyl-1H-imidazol-2-ylmethyl)pyrimidine-4-carboxamide (340 mg, 0.82 mmol) in MeOH (20 mL) at 0° C. was treated dropwise with conc HCl (4 mL), stirred at 80° C. for 1 h, cooled to room temperature and concentrated in vacuo. The residue was triturated with diethyl ether and the resulting dihydrochloride salt (230 mg, 78%) filtered, washed with diethyl ether, stirred with saturated aqueous NaHCO3 (5 mL), filtered and washed with water to give the title compound (165 mg, 71%) as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with diethyl ether
  4. filtrationthe resulting dihydrochloride salt (230 mg, 78%) filtered
  5. washwashed with diethyl ether
  6. stirringstirred with saturated aqueous NaHCO3 (5 mL)
  7. filtrationfiltered
  8. washwashed with water

Sources & evidence

ORD record
ord-6b62629ca9e34ddebb535397e853d71d
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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